Certain substituted 9,10-dioxo-9,10-dihydroanthrecene and 6H-anthra[1,9-cd]isoxazol-6-one heterocyclic compounds of Formula I:
and a process of preparing such compounds have been disclosed by Wu et al. (Wu et al., U.S. Publication No. 2015/0218132). A representative process for preparing compounds of Formula I, disclosed in Wu et al., is shown in Scheme 1:

The above process employs potentially unstable intermediates that can undergo exothermic decompositions (compound 3a; Steps 2 and 3) (Wedlich, R. C., Reduce Thermal Risk in Industrial Synthesis, CEPMagazine, October 2001, 60-65 and Fulton, J. R. et al., The Use of Tosylhydrazone Salts as a Safe Alternative for Handling Diazo Compounds and Their Application in Organic Synthesis, Eur. J. Org. Chem. 1:1479-1492 (2005)), the use of sodium azide which is highly toxic and poisonous (Step 3) (Chang, S and Lamm, S. H., Human Health Effects of Sodium Azide Exposure: A Literature Review and Analysis, Int. J. of Toxicology, 22:175-186 (2003)), and the production of compounds that contain azide substituents which are also potentially toxic and poisonous (compound 3) (Chang et al.). The process also goes through seven steps to produce the desired product (See Scheme 1). The lengthy synthesis and the hazardous reaction conditions result in a process that is both inefficient from economic perspective and also potentially dangerous to whoever carry out the process.
Certain compounds of Formula IV:
and a process of preparing such compounds were also disclosed by Wu et al. A representative process to synthesize compounds of Formula IV is shown in Scheme 1 (e.g., Compound 6 in Scheme 1) (see also Wu, U.S. Patent Publication 2015/0218132). Thus, the preparation of compounds of Formula IV is subject to the same disadvantages as the process for preparing compounds of Formula I.
It is also known that the compounds of Formula I and Formula IV can act as protein kinase inhibitors and/or antagonists. In particular, the compounds are described as Nerve Growth Factor (NGF) receptor Tyrosine receptor kinase A (TrkA) inhibitors and/or antagonists that can be used for the treatment and/or prevention of certain types of cancers, itching, atopic dermatitis, scabies, pityriasis, inflammation, restenosis, atherosclerosis, psoriasis, thrombosis, Alzheimer's, pain, a disease, disorder, injury, or malfunction relating to dysmyelination or demyelination or the disease or disorder associated with abnormal activities of protein kinases (Wu et al., WO 2010/077680, Wu et al., U.S. Pat. No. 9,040,508, and Wu et al., U.S. Publication No. 2015/0218132).
Thus, there is a need for technically simple and economic processes for the synthesis of the compounds of Formula I and Formula IV.